New synthetic protocol with trifluoro-1-propynylamines. An efficient access to α-(trifluoromethyl)-δ-keto amides via hetero diels-alder reaction

Chemistry Letters

Volumn , Issue 6, 2000, Pages 666-667

  Mantani, Toshiya ^a   Konno, Tsutomu ^a   Ishihara, Takashi ^a   Yamanaka, Hiroki ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034335855     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.666     Document Type: Article

References (17)

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2. For the methods with trifluoromethylated building blocks, see: T. Yokozawa, T. Nakai, and N. Ishikawa, Tetrahedron Lett., 25, 3987 (1984); T. S. Everett, S. T. Purrington, and C. L. Bumgardner, J. Org. Chem., 49, 3702 (1984); T. Yokozawa, T. Nakai, and N. Ishikawa, Chem. Lett., 1987, 1971; G. Shi and Y. Xu, J. Org. Chem., 55, 3383 (1990).
3. For the methods with trifluoromethylated building blocks, see: T. Yokozawa, T. Nakai, and N. Ishikawa, Tetrahedron Lett., 25, 3987 (1984); T. S. Everett, S. T. Purrington, and C. L. Bumgardner, J. Org. Chem., 49, 3702 (1984); T. Yokozawa, T. Nakai, and N. Ishikawa, Chem. Lett., 1987, 1971; G. Shi and Y. Xu, J. Org. Chem., 55, 3383 (1990).
4. For the methods with trifluoromethylated building blocks, see: T. Yokozawa, T. Nakai, and N. Ishikawa, Tetrahedron Lett., 25, 3987 (1984); T. S. Everett, S. T. Purrington, and C. L. Bumgardner, J. Org. Chem., 49, 3702 (1984); T. Yokozawa, T. Nakai, and N. Ishikawa, Chem. Lett., 1987, 1971; G. Shi and Y. Xu, J. Org. Chem., 55, 3383 (1990).
5. For the methods via trifluoromethylation, see: K. Iseki, T. Nagai, and Y. Kobayashi, Tetrahedron: Asymmetry, 5, 961 (1994); Y. Dan-oh and K. Uneyama, Bull. Chem. Soc. Jpn., 68, 2993 (1995).
6. For the methods via trifluoromethylation, see: K. Iseki, T. Nagai, and Y. Kobayashi, Tetrahedron: Asymmetry, 5, 961 (1994); Y. Dan-oh and K. Uneyama, Bull. Chem. Soc. Jpn., 68, 2993 (1995).
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10. T. Mantani, K. Shiomi, T. Ishihara, and H. Yamanaka, Chem. Lett., 1999, 855.
11. For the [4+2] cycloaddition of fluorine-free 1-alkynylamines, see: J. Ficini, J. Besseyre, and A. Krief, Bull. Chim. Soc. Fr., 1976, 987; J. Ficini, Tetrahedron, 32, 1449 (1976); J. Collard-Motte and Z. Janousek, Top. Curr. Chem., 130, 89 (1986); A. Padwa, Y. Gareau, B. Harrison, and A. Rodriguez, J. Org. Chem., 57, 3540 (1992).
12. For the [4+2] cycloaddition of fluorine-free 1-alkynylamines, see: J. Ficini, J. Besseyre, and A. Krief, Bull. Chim. Soc. Fr., 1976, 987; J. Ficini, Tetrahedron, 32, 1449 (1976); J. Collard-Motte and Z. Janousek, Top. Curr. Chem., 130, 89 (1986); A. Padwa, Y. Gareau, B. Harrison, and A. Rodriguez, J. Org. Chem., 57, 3540 (1992).
13. For the [4+2] cycloaddition of fluorine-free 1-alkynylamines, see: J. Ficini, J. Besseyre, and A. Krief, Bull. Chim. Soc. Fr., 1976, 987; J. Ficini, Tetrahedron, 32, 1449 (1976); J. Collard-Motte and Z. Janousek, Top. Curr. Chem., 130, 89 (1986); A. Padwa, Y. Gareau, B. Harrison, and A. Rodriguez, J. Org. Chem., 57, 3540 (1992).
14. For the [4+2] cycloaddition of fluorine-free 1-alkynylamines, see: J. Ficini, J. Besseyre, and A. Krief, Bull. Chim. Soc. Fr., 1976, 987; J. Ficini, Tetrahedron, 32, 1449 (1976); J. Collard-Motte and Z. Janousek, Top. Curr. Chem., 130, 89 (1986); A. Padwa, Y. Gareau, B. Harrison, and A. Rodriguez, J. Org. Chem., 57, 3540 (1992).
15. +, 13), 57 (100).
16. 2: M, 309.1915.
17. All products gave satisfactory spectral and analytical data.